Presentation Title

Synthesis of 1,2,3-Benzotriazole Derivatives Via Microwave Induced Gold Catalysis

Faculty Mentor

Robert Iafe

Start Date

17-11-2018 12:30 PM

End Date

17-11-2018 2:30 PM

Location

CREVELING 102

Session

POSTER 2

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

1,2,3-Benzotriazole derivatives play a significant role in the chemical and biological industries, particularly in pharmaceuticals. These compounds are of particular interest because the 1,2,3-benzotriazole motif is a common scaffold found in medicines that function as analgesic, antiviral, antifungal, and anticancer drugs. Herein, we present new methodology towards the synthesis of these benzotriazole derivatives using a gold(I) salt as a catalyst. The reaction involves 1,2,3-benzotriazole as the nucleophile and benzylic alcohols as the electrophile. Microwave irradiation allows this one-step reaction to be completed in only six hours. Our reaction protocol results in higher yield and regioselectivity than conventional heating techniques. All products are isolated by column chromatography and analyzed using 1H-NMR. Reaction optimization and substrate scope investigation will be presented.

Summary of research results to be presented

The gold(I)-catalyzed electrophilic aromatic substitution-type reaction has been optimized using 1,2,3-benzotriazole as the nucleophile, phenylethanol as the electrophile, 5 mol % of the gold(I) and silver(I) salts, and slightly elevated temperatures to afford 92% of the target 1,2,3-benzotriazole derivative. Using these conditions, the substrate scope for this reaction was explored using electron rich and electron deficient electrophiles. Reaction yields of 12 different substrates ranged from 49% (1-naphthylethanol) to 92% (1-(4-methoxyphenyl)ethanol). Furthermore, data from the substrate scope investigation supports a gold mechanism that involves a carbocation instead of a gold carbene intermediate. Example synthesis utilizing this reaction protocol of a small molecule cancer drug will also be presented.

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Nov 17th, 12:30 PM Nov 17th, 2:30 PM

Synthesis of 1,2,3-Benzotriazole Derivatives Via Microwave Induced Gold Catalysis

CREVELING 102

1,2,3-Benzotriazole derivatives play a significant role in the chemical and biological industries, particularly in pharmaceuticals. These compounds are of particular interest because the 1,2,3-benzotriazole motif is a common scaffold found in medicines that function as analgesic, antiviral, antifungal, and anticancer drugs. Herein, we present new methodology towards the synthesis of these benzotriazole derivatives using a gold(I) salt as a catalyst. The reaction involves 1,2,3-benzotriazole as the nucleophile and benzylic alcohols as the electrophile. Microwave irradiation allows this one-step reaction to be completed in only six hours. Our reaction protocol results in higher yield and regioselectivity than conventional heating techniques. All products are isolated by column chromatography and analyzed using 1H-NMR. Reaction optimization and substrate scope investigation will be presented.